WO2021255073A1 - Organic molecules for optoelectronic devices - Google Patents

Organic molecules for optoelectronic devices Download PDF

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Publication number
WO2021255073A1
WO2021255073A1 PCT/EP2021/066197 EP2021066197W WO2021255073A1 WO 2021255073 A1 WO2021255073 A1 WO 2021255073A1 EP 2021066197 W EP2021066197 W EP 2021066197W WO 2021255073 A1 WO2021255073 A1 WO 2021255073A1
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Prior art keywords
group
optionally substituted
organic
independently
deuterium
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PCT/EP2021/066197
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French (fr)
Inventor
Stefan Seifermann
Daniel Zink
Sebastian DÜCK
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Cynora Gmbh
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Priority to JP2022577431A priority Critical patent/JP2023530344A/en
Priority to CN202180042625.2A priority patent/CN115812074A/en
Priority to US18/009,965 priority patent/US20230303594A1/en
Priority to KR1020227041586A priority patent/KR20230027002A/en
Priority to EP21739259.6A priority patent/EP4168418A1/en
Publication of WO2021255073A1 publication Critical patent/WO2021255073A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
  • the object of the present invention is to provide molecules which are suitable for use in optoelectronic devices.
  • the organic molecules are purely organic molecules, i.e. they do not contain any metal ions in contrast to metal complexes known for the use in optoelectronic devices.
  • the organic molecules of the invention include metalloids, in particular B, Si, Sn, Se, and/or Ge.
  • the organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range.
  • the organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm.
  • the photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 50 % or more.
  • OLED organic light-emitting diode
  • Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.
  • organic light-emitting molecules according to the invention comprise or consist a structure of formula I, Formula I wherein either both groups T are R 1 or both groups V are R 1 while the group T or V that is not R 1 is selected from the group consisting of hydrogen, deuterium;
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph;
  • R 1 has a structure of the following formula F
  • Formula F i.e. a methyl group, which is substituted with two groups R 6 and one phenyl, which is optionally substituted with n R 6 , wherein n is an integer, which is at each occurrence selected from the group consisting of 0, 1 , 2, 3, 4 and 5; the dotted line in the formula F marks the bonding position to the structure shown in formula I;
  • R 6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, and
  • R 1 , R", R m , R IV , R v , R VI , R VM , R vm , R IX and R x is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium,
  • Ci-C 5 -alkoxy wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
  • Ci-C 5 -thioalkoxy wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
  • R XI is selected from the group consisting of hydrogen, chloride and C 1 -C 5 alkyl.
  • both groups T are R 1 or both groups V are R 1 . It is not possible that all variables T and V in formula I are R 1 .
  • the organic molecule of the invention comprises or consists of a structure selected from the group consisting of formula la and formula lb: Formula la wherein
  • V # is selected from the group consisting of hydrogen, deuterium,
  • Ci-C 5 -alkyl Ci-C 5 -alkyl
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
  • T # is selected from the group consisting of hydrogen, deuterium,
  • Ci-C 5 -alkyl Ci-C 5 -alkyl
  • R 1 is bonded via the position marked by the dotted line shown in formula F, which means, Formula la is identically represented by and formula lb is identically represented by
  • the organic molecule of the invention has at least two groups with a structure of formula F, but may have up to 12 groups with a structure of formula F. Certain embodiments of the organic molecule have two or four groups with a structure of formula F.
  • the organic molecules comprise or consist of a structure selected from the group consisting of formula la and formula lb, wherein T # and V # is selected from the group consisting of hydrogen, deuterium, Me, 'Pr, ‘Bu, and
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
  • T and V are selected from the group consisting of
  • R 1 hydrogen, deuterium, Me, 'Pr, ‘Bu, and
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
  • R 6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, Me, 'Pr, ‘Bu, and neo-pentyl.
  • R 6 is at each occurrence independently from each other selected from the group consisting of: hydrogen and Me.
  • R 1 is at each occurrence of the group consisting of formula R 1a and formula R 1b :
  • R 1 includes for example: In one particularly preferred embodiment, R 1 is selected from the group consisting of formula R 1c and formula R 1d :
  • R XI is selected from the group of hydrogen, Me, 'Pr and ‘Bu.
  • R XI is selected from the group of hydrogen or Me.
  • R XI is hydrogen
  • R XI is chloride
  • R XI is Me.
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R IX and R x is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 , SiMe 3 , SiPhb,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R lx and R x is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R IX and R x is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R IX and R x is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R IX and R x is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph) 2 .
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R lx and R x is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph) 2 .
  • R', R", R m , R IV , R v , R VI , R VM , R vm , R lx and R x is independently from another selected from the group consisting of: R 1 , hydrogen, ‘Bu, and Ph.
  • the organic molecules comprise or consist of a structure of formula II, wherein R 1 , R", R m , R IV , R v is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 , SiMe 3 , SiPhb,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • the organic molecules comprise or consist of formula II, wherein R', R", R m , R IV , R v is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • the organic molecules comprise or consist of formula II, wherein R', R", R m , R IV , R v is independently from another selected from the group consisting of:
  • R 1 hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph
  • triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  • the organic molecules comprise or consist of formula II, wherein R', R", R IM , R IV , R v is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph
  • carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  • the organic molecules comprise or consist of formula II, wherein R', R", R m , R IV , R v is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph) 2 .
  • the organic molecules comprise or consist of Formula II, wherein R', R", R m , R IV , R v is independently from another selected from the group consisting of: R 1 , hydrogen, deuterium, Me, 'Pr, ‘Bu,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph) 2 .
  • the organic molecules comprise or consist of formula II, wherein R', R", R m , R IV , R v is independently from another selected from the group consisting of: R 1 , hydrogen, ‘Bu, and Ph.
  • the organic molecules comprise or consist of a structure selected from the group consisting of formula 11-1 and formula II-2:
  • Formula 11-1 Formula II-2
  • the organic molecules according to the invention which comprise or consist of a structure selected from the group consisting of formula 11-1 and formula II-2:
  • the organic molecules comprise or consist of a structure selected from the group consisting of formula I la, formula lib, formula lie, and formula lid:
  • organic molecules comprising or consisting of a structure selected from the group consisting of formula lla, formula lib, formula lie, and formula lid are shown below:
  • the organic molecules comprise or consist of a structure selected from the group consisting of formula Ilia and formula Nib:
  • the organic molecules comprise or consist of a structure selected from the group consisting of formula llla-1 and formula lllb-1:
  • the organic molecule comprises or consists of a structure selected from the group consisting of formula IV-1 and formula IV-2: Formula IV-1
  • the organic molecule comprises or consists of a structure selected from the group consisting of formula IVa and formula IVb:
  • the organic molecule comprises or consists of a structure selected from the group consisting of formula IV-3 and formula IV-4:
  • the organic molecule comprises or consists of a structure selected from the group consisting of formula IVc and formula IVd:
  • aryl and aromatic may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties. Accordingly, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Notwithstanding, throughout the application the number of aromatic ring atoms may be given as subscripted number in the definition of certain substituents. In particular, the heteroaromatic ring includes one to three heteroatoms.
  • heteroaryl and “heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom.
  • the heteroatoms may at each occurrence be the same or different and be individually selected from the group consisting of N, O and S.
  • arylene refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure.
  • a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied.
  • a condensed (annulated) aromatic or heteroaromatic polycycle is built of two or more single aromatic or heteroaromatic cycles, which formed the polycycle via a condensation reaction.
  • aryl group or heteroaryl group comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiophene
  • cyclic group may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
  • biphenyl as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is defined in regard to the binding site to another chemical moiety.
  • alkyl group may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent.
  • alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl ( n Pr), i-propyl ('Pr), cyclopropyl, n-butyl ( n Bu), i- butyl ('Bu), s-butyl ( s Bu), t-butyl (‘Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2- pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopen
  • alkenyl comprises linear, branched, and cyclic alkenyl substituents.
  • alkenyl group comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
  • alkynyl comprises linear, branched, and cyclic alkynyl substituents.
  • alkynyl group for example, comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
  • alkoxy comprises linear, branched, and cyclic alkoxy substituents.
  • alkoxy group exemplarily comprises methoxy, ethoxy, n-propoxy, i- propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
  • thioalkoxy comprises linear, branched, and cyclic thioalkoxy substituents, in which the O of the exemplarily alkoxy groups is replaced by S.
  • halogen and “halo” may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine.
  • the organic molecules according to the invention have an excited state lifetime of not more than 150 ps, of not more than 100 ps, in particular of not more than 50 ps, more preferably of not more than 10 ps or not more than 7 ps in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature.
  • PMMA poly(methyl methacrylate)
  • the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e. , in the range of a wavelength of from 380 nm to 800 nm, with a full width at half maximum of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature.
  • PMMA poly(methyl methacrylate)
  • Orbital and excited state energies can be determined either by means of experimental methods.
  • the energy of the highest occupied molecular orbital E HOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV.
  • the energy of the lowest unoccupied molecular orbital E LUMO is calculated as E HOMO + E 9ap , wherein E 9ap is determined as follows: For host compounds, the onset of the emission spectrum of a film with 10 % by weight of host in poly(methyl methacrylate) (PMMA) is used as E 9ap , unless stated otherwise.
  • E 9ap is determined as the energy at which the excitation and emission spectra of a film with 10 % by weight of emitter in PMMA cross.
  • E 9ap is determined as the energy at which the excitation and emission spectra of a film with 2 % by weight of emitter in PMMA cross.
  • the energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, typically at 77 K.
  • the phosphorescence is usually visible in a steady-state spectrum in 2-Me-THF.
  • the triplet energy can thus be determined as the onset of the phosphorescence spectrum.
  • the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, if not otherwise stated, measured in a film of PMMA with 10 % by weight of emitter and in case of the organic molecules according to the invention with 2 % by weight of the organic molecules according to the invention.
  • the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum, if not otherwise stated, measured in a film of PMMA with 10 % by weight of host or emitter compound and in case of the organic molecules according to the invention with 2 % by weight of the organic molecules according to the invention.
  • the onset of an emission spectrum is determined by computing the intersection of the tangent to the emission spectrum with the x-axis.
  • the tangent to the emission spectrum is set at the high-energy side of the emission band and at the point at half maximum of the maximum intensity of the emission spectrum.
  • the organic molecules according to the invention have an onset of the emission spectrum, which is energetically close to the emission maximum, i.e. the energy difference between the onset of the emission spectrum and the energy of the emission maximum is below 0.14 eV, preferably below 0.13 eV, or even below 0.12 eV, while the full width at half maximum (FWHM) of the organic molecules is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature, resulting in a CIEy coordinate below 0.20, preferably below 0.18, more preferably below 0.16 or even more preferred below 0.14.
  • PMMA poly(methyl methacrylate)
  • a further aspect of the invention relates to the use of an organic molecule of the invention as a luminescent emitter or as an absorber, and/or as a host material and/or as an electron transport material, and/or as a hole injection material, and/or as a hole blocking material in an optoelectronic device.
  • a preferred embodiment relates to the use of an organic molecule according to the invention as a luminescent emitter in an optoelectronic device.
  • the optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e. , in the range of a wavelength of from 380 to 800 nm. More preferably, the optoelectronic device may be able to emit light in the visible range, i.e., of from 400 nm to 800 nm.
  • UV visible or nearest ultraviolet
  • the optoelectronic device is more particularly selected from the group consisting of:
  • OLEDs organic light-emitting diodes
  • the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
  • OLED organic light emitting diode
  • LEC light emitting electrochemical cell
  • the fraction of the organic molecule according to the invention in the emission layer in an optoelectronic device, more particularly in an OLED is 0.1 % to 99 % by weight, more particularly 1 % to 80 % by weight. In an alternative embodiment, the proportion of the organic molecule in the emission layer is 100 % by weight.
  • the light-emitting layer comprises not only the organic molecules according to the invention, but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.
  • a further aspect of the invention relates to a composition
  • a composition comprising or consisting of:
  • the light-emitting layer comprises (or essentially consists of) a composition comprising or consisting of:
  • the light-emitting layer EML comprises (or essentially consists of) a composition comprising or consisting of:
  • energy can be transferred from the host compound H to the one or more organic molecules according to the invention, in particular transferred from the first excited triplet state T 1 (H) of the host compound H to the first excited triplet state T 1 (E) of the one or more organic molecules according to the invention E and/ or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of the one or more organic molecules according to the invention E.
  • the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) in the range of from -5 to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D), wherein E HOMO (H) > E HOMO (D).
  • the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D), wherein E LUMO (H)
  • the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) and a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H)
  • the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D) and a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D)
  • the organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy E HOMO (E) and a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (E)
  • the host compound D and/ or the host compound H is a thermally-activated delayed fluorescence (TADF)-material.
  • TADF materials exhibit a AEST value, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), of less than 2500 crrr 1 .
  • the TADF material exhibits a AEST value of less than 3000 cm -1 , more preferably less than 1500 cm -1 , even more preferably less than 1000 cm -1 or even less than 500 cm -1 .
  • the host compound D is a TADF material and the host compound FI exhibits a AEST value of more than 2500 cm -1 .
  • the host compound D is a TADF material and the host compound FI is selected from group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9FI-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9FI-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9FI-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9FI-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9FI- carbazole.
  • the host compound FI is a TADF material and the host compound D exhibits a AEST value of more than 2500 cm -1 .
  • the host compound FI is a TADF material and the host compound D is selected from group consisting of T2T (2,4,6- tris(biphenyl-3-yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine) and/or TST (2,4,6-tris(9,9'-spirobifluorene-2-yl)-1,3,5-triazine).
  • the invention relates to an optoelectronic device comprising an organic molecule or a composition of the type described here, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, more particularly gas and vapour sensors not hermetically externally shielded, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
  • OLED organic light-emitting diode
  • OLED sensor more particularly gas and vapour sensors not hermetically externally shielded
  • organic diode organic solar cell
  • organic transistor organic field-effect transistor
  • organic laser and down-conversion element organic laser and down-conversion element
  • the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
  • OLED organic light emitting diode
  • LEC light emitting electrochemical cell
  • the organic molecule according to the invention E is used as emission material in a light-emitting layer EML.
  • the light-emitting layer EML consists of the composition according to the invention described here.
  • the optoelectronic device is an OLED, it may, for example, have the following layer structure: 1. substrate
  • cathode layer wherein the OLED comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL only optionally, different layers may be merged and the OLED may comprise more than one layer of each layer type defined above.
  • the optoelectronic device may, in one embodiment, comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, for example, moisture, vapor and/or gases.
  • the optoelectronic device is an OLED, with the following inverted layer structure:
  • the optoelectronic device is an OLED, which may have a stacked architecture. In this architecture, contrary to the typical arrangement in which the OLEDs are placed side by side, the individual units are stacked on top of each other. Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs.
  • the OLED exhibiting a stacked architecture may comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
  • CGL charge generation layer
  • the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode.
  • this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers.
  • the emission layers are adjacently stacked.
  • the tandem OLED comprises a charge generation layer between each two emission layers.
  • adjacent emission layers or emission layers separated by a charge generation layer may be merged.
  • the substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow for a higher degree of flexibility.
  • the anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent.
  • the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs).
  • Such anode layer A may, for example, comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
  • the anode layer A may consist of indium tin oxide (ITO) (e.g., (ln0 3 )o .9 (Sn0 2 )o .i ).
  • ITO indium tin oxide
  • the roughness of the anode layer A caused by the transparent conductive oxides (TCOs) may be compensated by using a hole injection layer (HIL).
  • HIL hole injection layer
  • the HIL may facilitate the injection of quasi charge carriers (i.e. , holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated.
  • the hole injection layer may comprise poly-3, 4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), M0O2, V2O5, CuPC or Cul, in particular a mixture of PEDOT and PSS.
  • the hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL).
  • the HIL may, for example, comprise PEDOT:PSS (poly-3, 4-ethylendioxy thiophene: polystyrene sulfonate), PEDOT (poly-3, 4-ethylendioxy thiophene), mMTDATA (4, 4', 4"- tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)- 9,9’-spirobifluorene), DNTPD (N1 ,NT-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m- tolylbenzene-1, 4-diamine), NPB (N,N'-nis-(1-naphthalenyl)-N,N'-bis-phenyl-(1 ,T-biphenyl)- 4,4
  • a hole transport layer Adjacent to the anode layer A or hole injection layer (HIL), a hole transport layer (HTL) is typically located.
  • HTL hole transport layer
  • any hole transport compound may be used.
  • electron- rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound.
  • the HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML.
  • the hole transport layer (HTL) may also be an electron blocking layer (EBL).
  • EBL electron blocking layer
  • hole transport compounds bear comparably high energy levels of their triplet states T1.
  • the hole transport layer may comprise a star-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4- butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4 - cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4',4"-tris[2- naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT- CN and/or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole).
  • TCTA tris(4-car
  • the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix.
  • Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may, for example, be used as inorganic dopant.
  • Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(l)pFBz) or transition metal complexes may, for example, be used as organic dopant.
  • the EBL may, for example, comprise mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-Butylphenyl)-3,6- bis(triphenylsilyl)-9H-carbazole), and/or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).
  • the light-emitting layer EML Adjacent to the hole transport layer (HTL), the light-emitting layer EML is typically located.
  • the light-emitting layer EML comprises at least one light emitting molecule.
  • the EML comprises at least one light emitting molecule according to the invention E.
  • the light-emitting layer comprises only the organic molecules according to the invention.
  • the EML additionally comprises one or more host materials H.
  • the host material H is selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2- yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole, 9-[3,5-bis(2-
  • the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host.
  • the EML comprises exactly one light emitting organic molecule according to the invention and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole as hole-dominant host.
  • the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 % by weight, preferably 15-30 % by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
  • a host selected from CBP, mCP, mCBP
  • an electron transport layer Adjacent to the light-emitting layer EML, an electron transport layer (ETL) may be located.
  • ETL electron transport layer
  • any electron transporter may be used.
  • electron-poor compounds such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole), phosphinoxides and sulfone, may be used.
  • An electron transporter may also be a star-shaped heterocycle such as 1, 3, 5-tri(1 -phenyl-1 H-benzo[d]imidazol-2-yl)phenyl (TPBi).
  • the ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3- yl)phenyl]benzene) and/or BTB (4, 4'-bis-[2-(4,6-diphenyl-1 , 3, 5-triazinyl)]-1,1 -biphenyl
  • a cathode layer C Adjacent to the electron transport layer (ETL), a cathode layer C may be located.
  • the cathode layer C may, for example, comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy.
  • the cathode layer may also consist of (essentially) intransparent metals such as Mg, Ca or Al.
  • the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs).
  • the cathode layer C may also consist of nanoscalic silver wires.
  • An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)).
  • This layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8- hydroxyquinolinolatolithium), LhO, BaF2, MgO and/or NaF.
  • the electron transport layer (ETL) and/or a hole blocking layer (HBL) may also comprise one or more host compounds H.
  • the light-emitting layer EM L may further comprise one or more further emitter molecules F.
  • Such an emitter molecule F may be any emitter molecule known in the art.
  • Preferably such an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention E.
  • the emitter molecule F may optionally be a TADF emitter.
  • the emitter molecule F may optionally be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML.
  • the triplet and/or singlet excitons may be transferred from the organic emitter molecule according to the invention to the emitter molecule F before relaxing to the ground state SO by emitting light typically red- shifted in comparison to the light emitted by an organic molecule.
  • the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
  • an optoelectronic device may, for example, be an essentially white optoelectronic device.
  • white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more molecules as described above.
  • the designation of the colors of emitted and/or absorbed light is as follows: violet: wavelength range of >380-420 nm; deep blue: wavelength range of >420-480 nm; sky blue: wavelength range of >480-500 nm; green: wavelength range of >500-560 nm; yellow: wavelength range of >560-580 nm; orange: wavelength range of >580-620 nm; red: wavelength range of >620-800 nm.
  • a deep blue emitter has an emission maximum in the range of from >420 to 480 nm
  • a sky blue emitter has an emission maximum in the range of from >480 to 500 nm
  • a green emitter has an emission maximum in a range of from >500 to 560 nm
  • a red emitter has an emission maximum in a range of from >620 to 800 nm.
  • a deep blue emitter may preferably have an emission maximum of below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.
  • a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m 2 of more than 8 %, more preferably of more than 10 %, more preferably of more than 13 %, even more preferably of more than 15 % or even more than 20 % and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/nT of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h.
  • a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.
  • a further aspect of the present invention relates to an OLED, which emits light at a distinct color point.
  • the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)).
  • FWHM full width at half maximum
  • the OLED according to the invention emits light with a FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV or even less than 0.17 eV.
  • UHD Ultra High Definition
  • a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a Cl Ey color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
  • the invention relates to a method for producing an optoelectronic component.
  • an organic molecule of the invention is used.
  • the optoelectronic device in particular the OLED according to the present invention can be fabricated by any means of vapor deposition and/ or liquid processing. Accordingly, at least one layer is prepared by means of a sublimation process, prepared by means of an organic vapor phase deposition process, prepared by means of a carrier gas sublimation process, solution processed or printed.
  • the methods used to fabricate the optoelectronic device, in particular the OLED according to the present invention are known in the art.
  • the different layers are individually and successively deposited on a suitable substrate by means of subsequent deposition processes. The individual layers may be deposited using the same or differing deposition methods.
  • Vapor deposition processes for example, comprise thermal (co) evaporation, chemical vapor deposition and physical vapor deposition.
  • an AMOLED backplane is used as substrate.
  • the individual layer may be processed from solutions or dispersions employing adequate solvents.
  • Solution deposition process for example, comprise spin coating, dip coating and jet printing.
  • Liquid processing may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may be completely or partially removed by means known in the state of the art.
  • trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to I3.
  • the corresponding boronic acid derivative of substrate 13 might be used as starting material under the same conditions.
  • reaction mixture After stirring for 30 minutes at rt, the reaction mixture is cooled to 0 °C and N,N-diisopropylethylamine (CAS: 7087-68-5, 3.00 equivalents) is added. The reaction mixture is allowed to warm to rt and then heated at reflux at 120 °C for 3h. Subsequently, the reaction mixture is poured into water and the resulting precipitate is filtered and washed with a minimum amount of ethyl acetate to obtain P1 as a solid product. P1 can be further purified by recrystallization or by flash chromatography.
  • N,N-diisopropylethylamine CAS: 7087-68-5, 3.00 equivalents
  • Boronic acid ester 16 is obtained according to AAV3 using compound 15 as the starting material.
  • trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 16.
  • Target compound P2 is synthesized according to AAV4 using boronic acid ester I6 as the starting material.
  • the boronic acid corresponding to I6 can be used as the starting material for the synthesis of P2.
  • Compound I9 is synthesized according to AAV9.
  • boronicacid ester 110 is carried out as described within AAV3 using precursor I9 as the substrate.
  • trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 110.
  • Target compound P3 is synthesized according to AAV4 using boronic acid ester 110 as the starting material.
  • the boronic acid corresponding to 110 might be used as the starting material for the synthesis of P3.
  • the synthesis of the target P3 is conducted via a one-pot protocol, where the chloride precursor 19 is directly converted into P3 following the procedure described within AAV5.
  • dichloro derivative I2-CI is synthesized from I2-CI following the procedure of AAV3, wherein alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to I3-CI.
  • the para- chloro derivative P1-CI is synthesized from P1-CI as described within AAV4.
  • the corresponding boronic acid derivative of substrate I3-CI might be used as starting material yielding P1-CI.
  • Compound I4-CI was synthesized accordingly to procedure AAV6 where 1,3-dibromo-2,5- dichlorobenzene (1.0 equivalent, CAS 81067-41-6) and primary amine E1 were used as the reactants.
  • Compound 15-CI is obtained by following the procedure AAV7 using secondary bisamine 14-CI and 1-bromo-3,5-diphenylbenzene (CAS: 103068-20-8) as the reactants.
  • Boronic acid ester 16-CI is obtained according to AAV3 using compound 15-CI as the starting material.
  • trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 16-CI.
  • the synthesis of P2-CI is conducted as described in AAV5 using I5-CI as the substrate.
  • the target material P2 is synthesized as described in AAV10 using P2-CI as the starting material.
  • Compound I8-CI is synthesized as described within AAV8, where 1-bromo-2, 3,5- trichlorobenzene (1.0 equivalent) and primary amine 17.1 were used as the reactants.
  • Compound I9-CI is synthesized from I7.2 and I8-CI according to AAV9.
  • the synthesis of boronic acid ester 110-CI is carried out as described within AAV3 using precursor I9-CI as the substrate.
  • trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 110-CI.
  • Compound P3-CI is synthesized according to AAV4 using boronic acid ester 110-CI as the starting material.
  • the boronic acid corresponding to 110-CI might be used as the starting material for the synthesis of P3-CI.
  • the target material P3 is synthesized as described in AAV10 using P3-CI as the starting material.
  • Cyclic voltammograms are measured from solutions having concentration of 10 3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate).
  • the measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2 + as internal standard.
  • the HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).
  • Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods.
  • Orbital and excited state energies are calculated with the B3LYP functional.
  • Def2-SVP basis sets and a m4-grid for numerical integration are used.
  • the Turbomole program package is used for all calculations.
  • Sample pretreatment Spin-coating Apparatus: Spin150, SPS euro.
  • the sample concentration is 10 mg/ml, dissolved in a suitable solvent.
  • Photoluminescence spectroscopy and Time-Correlated Single-Photon Counting Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
  • Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.
  • NanoLED 370 (wavelength: 371 nm, puls duration: 1,1 ns)
  • NanoLED 290 (wavelength: 294 nm, puls duration: ⁇ 1 ns)
  • SpectraLED 355 (wavelength: 355 nm).
  • Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.
  • Emission maxima are given in nm, quantum yields F in % and CIE coordinates as x,y values.
  • PLQY is determined using the following protocol:
  • Excitation wavelength the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength
  • Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation: wherein n Photon denotes the photon count and Int. the intensity.
  • Optoelectronic devices in particular OLED devices, comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
  • the not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current.
  • the OLED device lifetime is extracted from the change of the luminance during operation at constant current density.
  • the LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance
  • analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80 % of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95 % of the initial luminance etc.
  • Accelerated lifetime measurements are performed (e.g. applying increased current densities).
  • LT80 values at 500 cd/m 2 are determined using the following equation: wherein Lo denotes the initial luminance at the applied current density.
  • the values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
  • HPLC-MS analysis is performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).
  • Exemplarly a typical HPLC method is as follows: a reverse phase column 4,6mm x 150mm, particle size 3,5 pm from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6 x 150 mm, 3.5 pm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients
  • Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI +) or negative (APCI -) ionization mode.
  • APCI atmospheric pressure chemical ionization
  • Example 1 was synthesized according to
  • AAV1 (49% yield), wherein 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) as E1;
  • the emission maximum of example 1 (2% by weight in PMMA) is at 464 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.12 and the PLQY is 73%.
  • the onset of the emission spectrum is determined at 2.79 eV.
  • AAV1 (49% yield), wherein 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) as E1;
  • AAV2 (69% yield), wherein 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) was used as reactant E3; and AAV5 (13% yield).
  • the emission maximum of example 2 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.11 and the PLQY is 76%.
  • the onset of the emission spectrum is determined at 2.79 eV.
  • Example 1 was synthesized according to
  • AAV2 (83% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) and 4,4'- bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and 11, respectively;
  • AAV3 (32% yield), wherein trimethyl borate (CAS 121-43-7) was used as the borylating reagent and wherein the corresponding boronic acid derivative of I3 was obtained; and AAV4 (23% yield).
  • Example 4 The emission maximum of example 3 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.16 eV, the CIEy coordinate is 0.10 and the PLQY is 80%. The onset of the emission spectrum is determined at 2.79 eV.
  • Example 4 The emission maximum of example 3 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.16 eV, the CIEy coordinate is 0.10 and the PLQY is 80%. The onset of the emission spectrum is determined at 2.79 eV.
  • FWHM full width at half maximum
  • Example 4 was synthesized according to
  • AAV2 (72% yield), wherein 4-Chloro-3,5-dibromotoluene (CAS 202925-05-1) and 4,4'- bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and 11, respectively;
  • AAV3 (50% yield), wherein trimethyl borate (CAS 121-43-7) was used as the borylating reagent and wherein the corresponding dichloride I2-CI was used as the reactant and wherein the corresponding boronic acid derivative of I3-CI was obtained;
  • AAV4 (58% yield); and AAV10 (81% yield), wherein the corresponding starting material P1-CI was reacted with methaneboronic acid (CAS: 13061-96-6).
  • the emission maximum of example 4 (2% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.10 and the PLQY is 81%.
  • the onset of the emission spectrum is determined at 2.81 eV.
  • Example 1 was tested in the OLED D1 , which was fabricated with the following layer structure:
  • OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m 2 of 12.1%.
  • the emission maximum is at 468 nm with a FWHM of 26 nm at 3.6 V.
  • the corresponding CIEy value is 0.12.
  • Example 2 was tested in the OLED D2, which was fabricated with the following layer structure:
  • OLED D2 yielded an external quantum efficiency (EQE) at 1000 cd/m 2 of 10.9%.
  • the emission maximum is at 464 nm with a FWHM of 28 nm at 3.8 V.
  • the corresponding CIEy value is 0.10.
  • Example 3 was tested in the OLED D3, which was fabricated with the following layer structure:
  • OLED D3 yielded an external quantum efficiency (EQE) at 1000 cd/m 2 of 11.8%.
  • the emission maximum is at 466 nm with a FWHM of 26 nm at 3.5 V.
  • the corresponding CIEy value is 0.10.
  • Example 4 was tested in the OLED D4, which was fabricated with the following layer structure: OLED D4 yielded an external quantum efficiency (EQE) at 1000 cd/m 2 of 11.2%. The emission maximum is at 464 nm with a FWHM of 26 nm at 3.6 V. The corresponding CIEy value is 0.09.
  • EQE external quantum efficiency

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Abstract

The invention relates to an organic molecule for the application in optoelectronic devices. According to the invention, the organic molecule has a structure of formula (I): wherein either both groups T are R1 or both groups V are R1 while the group T or V that is not R1 is selected from the group consisting of hydrogen, deuterium, R1, C1-C5-alkyl, and Ph (= phenyl), which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph; R1 is methyl, which is substituted with two groups R6 and one phenyl, which is optionally substituted with R6:, which is bonded via the position marked by the dotted line; and n is an integer, which is selected from the group consisting of 0, 1, 2, 3, 4 and 5.

Description

ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES
The invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
Description
The object of the present invention is to provide molecules which are suitable for use in optoelectronic devices.
This object is achieved by the invention which provides a new class of organic molecules.
According to the invention the organic molecules are purely organic molecules, i.e. they do not contain any metal ions in contrast to metal complexes known for the use in optoelectronic devices. The organic molecules of the invention, however, include metalloids, in particular B, Si, Sn, Se, and/or Ge.
According to the present invention, the organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 50 % or more. The use of the molecules according to the invention in an optoelectronic device, for example an organic light-emitting diode (OLED), leads to higher efficiencies or higher color purity, expressed by the full width at half maximum (FWHM) of emission, of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.
The organic light-emitting molecules according to the invention comprise or consist a structure of formula I, Formula I wherein either both groups T are R1 or both groups V are R1 while the group T or V that is not R1 is selected from the group consisting of hydrogen, deuterium;
Ci-C5-alkyl; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph; wherein
R1 has a structure of the following formula F
Figure imgf000003_0001
Formula F i.e. a methyl group, which is substituted with two groups R6and one phenyl, which is optionally substituted with n R6, wherein n is an integer, which is at each occurrence selected from the group consisting of 0, 1 , 2, 3, 4 and 5; the dotted line in the formula F marks the bonding position to the structure shown in formula I;
R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, and
Ci-C5-alkyl;
R1, R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of: R1, hydrogen, deuterium,
N(R5)2,
OR5,
SR5,
Si(R5)s,
B(OR5)2,
OSO2R5,
CFs,
CN, halogen,
CrC4o-alkyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C40-thioalkoxy, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5; Ce-Ceo-aryl, which is optionally substituted with one or more substituents R5; and C3-C57-heteroaryl, which is optionally substituted with one or more substituents R5;
R5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh (Ph = phenyl), SPh, CF3, CN, F, Si(Ci-Cs-alkyl)3, Si(Ph)3, Ci-C5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-C5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-C5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C6-Ci8-aryl, which is optionally substituted with one or more CrCs-alkyl substituents;
C3-C17-heteroaryl, which is optionally substituted with one or more CrCs-alkyl substituents; N(C6-Ci8-aryl)2,
N(C3-Ci7-heteroaryl)2; and N(C3-Ci7-heteroaryl)(C6-Ci8-aryl).
RXI is selected from the group consisting of hydrogen, chloride and C1-C5 alkyl.
According to the invention, either both groups T are R1 or both groups V are R1. It is not possible that all variables T and V in formula I are R1.
Put differently, the organic molecule of the invention comprises or consists of a structure selected from the group consisting of formula la and formula lb: Formula la wherein
V# is selected from the group consisting of hydrogen, deuterium,
Ci-C5-alkyl; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
Figure imgf000006_0001
Formula lb wherein
T# is selected from the group consisting of hydrogen, deuterium,
Ci-C5-alkyl; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph. According to the invention, R1 is bonded via the position marked by the dotted line shown in formula F, which means, Formula la is identically represented by
Figure imgf000007_0001
and formula lb is identically represented by
Figure imgf000007_0002
The organic molecule of the invention has at least two groups with a structure of formula F, but may have up to 12 groups with a structure of formula F. Certain embodiments of the organic molecule have two or four groups with a structure of formula F.
In a preferred embodiment, the organic molecules comprise or consist of a structure selected from the group consisting of formula la and formula lb, wherein T# and V# is selected from the group consisting of hydrogen, deuterium, Me, 'Pr, ‘Bu, and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
In a preferred embodiment, T and V are selected from the group consisting of
R1; hydrogen, deuterium, Me, 'Pr, ‘Bu, and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
Depending on the value of the integer n, R1 may have a structure as shown below: for n = 0:
Figure imgf000008_0001
for n = 4 wherein R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, and CrCs-alkyl, wherein, in certain embodiments, the Ci- C5-alkyl group may be Me, 'Pr, ‘Bu, or neo-pentyl.
In certain embodiments, R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, Me, 'Pr, ‘Bu, and neo-pentyl.
In other embodiments, R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen and Me.
In a preferred embodiment, R1 is at each occurrence of the group consisting of formula R1a and formula R1b:
Figure imgf000009_0001
Formula R1a Formula R1b.
Specific examples of R1 include for example:
Figure imgf000009_0002
In one particularly preferred embodiment, R1 is selected from the group consisting of formula R1c and formula R1d:
Figure imgf000010_0001
Formula R1c Formula R1d.
In one embodiment, RXI is selected from the group of hydrogen, Me, 'Pr and ‘Bu.
In one embodiment, RXI is selected from the group of hydrogen or Me.
In one embodiment, RXI is hydrogen.
In one embodiment, RXI is chloride.
In one embodiment, RXI is Me.
In one embodiment of the organic molecule, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3, SiMe3, SiPhb,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, Rlx and Rxis independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph)2.
In one embodiment, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, Rlx and Rxis independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph)2.
In one embodiment, R', R", Rm, RIV, Rv, RVI, RVM, Rvm, Rlx and Rxis independently from another selected from the group consisting of: R1, hydrogen, ‘Bu, and Ph.
In one embodiment of the invention, Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI which yields an organic molecule comprising or consisting of a structure of formula II:
Figure imgf000012_0001
Formula II
In one embodiment, the organic molecules comprise or consist of a structure of formula II, wherein R1, R", Rm, RIV, Rv is independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3, SiMe3, SiPhb,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, the organic molecules comprise or consist of formula II, wherein R', R", Rm, RIV, Rvis independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, the organic molecules comprise or consist of formula II, wherein R', R", Rm, RIV, Rv is independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2. In one embodiment, the organic molecules comprise or consist of formula II, wherein R', R", RIM, RIV, Rv is independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
In one embodiment, the organic molecules comprise or consist of formula II, wherein R', R", Rm, RIV, Rv is independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph)2.
In one embodiment, the organic molecules comprise or consist of Formula II, wherein R', R", Rm, RIV, Rvis independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph)2.
In one embodiment, the organic molecules comprise or consist of formula II, wherein R', R", Rm, RIV, Rv is independently from another selected from the group consisting of: R1, hydrogen, ‘Bu, and Ph.
In one embodiment, the organic molecules comprise or consist of a structure selected from the group consisting of formula 11-1 and formula II-2:
Figure imgf000014_0001
Formula 11-1 Formula II-2 Examples of the organic molecules according to the invention, which comprise or consist of a structure selected from the group consisting of formula 11-1 and formula II-2:
Figure imgf000015_0001
In certain embodiments of the invention, the organic molecules comprise or consist of a structure selected from the group consisting of formula I la, formula lib, formula lie, and formula lid:
Figure imgf000016_0001
Examples for organic molecules comprising or consisting of a structure selected from the group consisting of formula lla, formula lib, formula lie, and formula lid are shown below: In one embodiment, the organic molecules comprise or consist of a structure selected from the group consisting of formula Ilia and formula Nib:
Figure imgf000017_0001
Formula Ilia Formula Nib. In a preferred embodiment, the organic molecules comprise or consist of a structure selected from the group consisting of formula llla-1 and formula lllb-1:
Figure imgf000018_0001
Formula lllb-1.
In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formula IV-1 and formula IV-2:
Figure imgf000018_0002
Formula IV-1
Figure imgf000019_0001
In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formula IVa and formula IVb:
Figure imgf000019_0002
Formula IVb. In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formula IV-3 and formula IV-4:
Figure imgf000020_0001
Formula IV-4.
In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formula IVc and formula IVd:
Figure imgf000020_0002
Formula IVc Formula IVd.
As used throughout the present application, the terms "aryl" and "aromatic" may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties. Accordingly, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Notwithstanding, throughout the application the number of aromatic ring atoms may be given as subscripted number in the definition of certain substituents. In particular, the heteroaromatic ring includes one to three heteroatoms. Again, the terms “heteroaryl" and “heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom. The heteroatoms may at each occurrence be the same or different and be individually selected from the group consisting of N, O and S. Accordingly, the term "arylene" refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure. In case, a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied. According to the invention, a condensed (annulated) aromatic or heteroaromatic polycycle is built of two or more single aromatic or heteroaromatic cycles, which formed the polycycle via a condensation reaction.
In particular, as used throughout, the term “aryl group or heteroaryl group” comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole, 1 ,2-thiazole, 1,3- thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1 ,3,5- triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4- oxadiazole, 1,2,5-oxadiazole, 1 ,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or combinations of the abovementioned groups.
As used throughout, the term “cyclic group” may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
As used throughout, the term “biphenyl” as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is defined in regard to the binding site to another chemical moiety.
As used throughout, the term “alkyl group” may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent. In particular, the term alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl (nPr), i-propyl ('Pr), cyclopropyl, n-butyl (nBu), i- butyl ('Bu), s-butyl (sBu), t-butyl (‘Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2- pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methyl pentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2- bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl,
1.1-dimethyl-n-hex-1-yl, 1 , 1 -dimethyl-n-hept-1 -yl, 1 ,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec- 1-yl, 1,1-dimethyl-n-dodec-1-yl, 1 ,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl,
1.1-dimethyl-n-octadec-1-yl, 1 , 1 -diethyl-n-hex-1 -yl, 1 , 1 -diethyl-n-hept-1 -yl, 1 , 1 -diethyl-n-oct-1 - yl, 1 , 1 -diethyl-n-dec-1 -yl, 1,1-diethyl-n-dodec-1-yl, 1 , 1 -diethyl-n-tetradec-1 -yl, 1 , 1 -diethyln-n- hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.
As used throughout, the term “alkenyl” comprises linear, branched, and cyclic alkenyl substituents. The term “alkenyl group”, for example, comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
As used throughout, the term “alkynyl” comprises linear, branched, and cyclic alkynyl substituents. The term “alkynyl group”, for example, comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. As used throughout, the term “alkoxy” comprises linear, branched, and cyclic alkoxy substituents. The term “alkoxy group” exemplarily comprises methoxy, ethoxy, n-propoxy, i- propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
As used throughout, the term “thioalkoxy” comprises linear, branched, and cyclic thioalkoxy substituents, in which the O of the exemplarily alkoxy groups is replaced by S.
As used throughout, the terms “halogen” and “halo” may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine.
Whenever hydrogen (H) is mentioned herein, it could also be replaced by deuterium at each occurrence.
It is understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as if it were the whole molecule (e.g. naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.
In one embodiment, the organic molecules according to the invention have an excited state lifetime of not more than 150 ps, of not more than 100 ps, in particular of not more than 50 ps, more preferably of not more than 10 ps or not more than 7 ps in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature.
In a further embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e. , in the range of a wavelength of from 380 nm to 800 nm, with a full width at half maximum of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature.
Orbital and excited state energies can be determined either by means of experimental methods. The energy of the highest occupied molecular orbital EHOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV. The energy of the lowest unoccupied molecular orbital ELUMO is calculated as EHOMO + E9ap, wherein E9ap is determined as follows: For host compounds, the onset of the emission spectrum of a film with 10 % by weight of host in poly(methyl methacrylate) (PMMA) is used as E9ap, unless stated otherwise. For emitter molecules, E9ap is determined as the energy at which the excitation and emission spectra of a film with 10 % by weight of emitter in PMMA cross. For the organic molecules according to the invention, E9ap is determined as the energy at which the excitation and emission spectra of a film with 2 % by weight of emitter in PMMA cross.
The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, typically at 77 K. For host compounds, where the first excited singlet state and the lowest triplet state are energetically separated by > 0.4 eV, the phosphorescence is usually visible in a steady-state spectrum in 2-Me-THF. The triplet energy can thus be determined as the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, if not otherwise stated, measured in a film of PMMA with 10 % by weight of emitter and in case of the organic molecules according to the invention with 2 % by weight of the organic molecules according to the invention. Both for host and emitter compounds, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum, if not otherwise stated, measured in a film of PMMA with 10 % by weight of host or emitter compound and in case of the organic molecules according to the invention with 2 % by weight of the organic molecules according to the invention.
The onset of an emission spectrum is determined by computing the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set at the high-energy side of the emission band and at the point at half maximum of the maximum intensity of the emission spectrum.
In one embodiment, the organic molecules according to the invention have an onset of the emission spectrum, which is energetically close to the emission maximum, i.e. the energy difference between the onset of the emission spectrum and the energy of the emission maximum is below 0.14 eV, preferably below 0.13 eV, or even below 0.12 eV, while the full width at half maximum (FWHM) of the organic molecules is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV in a film of poly(methyl methacrylate) (PMMA) with 2 % by weight of organic molecule at room temperature, resulting in a CIEy coordinate below 0.20, preferably below 0.18, more preferably below 0.16 or even more preferred below 0.14. A further aspect of the invention relates to the use of an organic molecule of the invention as a luminescent emitter or as an absorber, and/or as a host material and/or as an electron transport material, and/or as a hole injection material, and/or as a hole blocking material in an optoelectronic device.
A preferred embodiment relates to the use of an organic molecule according to the invention as a luminescent emitter in an optoelectronic device.
The optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e. , in the range of a wavelength of from 380 to 800 nm. More preferably, the optoelectronic device may be able to emit light in the visible range, i.e., of from 400 nm to 800 nm.
In the context of such use, the optoelectronic device is more particularly selected from the group consisting of:
• organic light-emitting diodes (OLEDs),
• light-emitting electrochemical cells,
• OLED sensors, especially in gas and vapor sensors that are not hermetically shielded to the surroundings,
• organic diodes,
• organic solar cells,
• organic transistors,
• organic field-effect transistors,
• organic lasers, and
• down-conversion elements.
In a preferred embodiment in the context of such use, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In the case of the use, the fraction of the organic molecule according to the invention in the emission layer in an optoelectronic device, more particularly in an OLED, is 0.1 % to 99 % by weight, more particularly 1 % to 80 % by weight. In an alternative embodiment, the proportion of the organic molecule in the emission layer is 100 % by weight.
In one embodiment, the light-emitting layer comprises not only the organic molecules according to the invention, but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.
A further aspect of the invention relates to a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and
(b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and
(c) optional one or more dyes and/or one or more solvents.
In one embodiment, the light-emitting layer comprises (or essentially consists of) a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and
(b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and
(c) optional one or more dyes and/or one or more solvents.
In a particular embodiment, the light-emitting layer EML comprises (or essentially consists of) a composition comprising or consisting of:
(i) 0.1-10 % by weight, preferably 0.5-5 % by weight, in particular 1-3 % by weight, of one or more organic molecules according to the invention;
(ii) 5-99 % by weight, preferably 15-85 % by weight, in particular 20-75% by weight, of at least one host compound H; and
(iii) 0.9-94.9 % by weight, preferably 14.5-80 % by weight, in particular 24-77 % by weight, of at least one further host compound D with a structure differing from the structure of the molecules according to the invention; and
(iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and
(v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention.
Preferably, energy can be transferred from the host compound H to the one or more organic molecules according to the invention, in particular transferred from the first excited triplet state T 1 (H) of the host compound H to the first excited triplet state T 1 (E) of the one or more organic molecules according to the invention E and/ or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of the one or more organic molecules according to the invention E.
In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy EHOMO(H) in the range of from -5 to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy EHOMO(D), wherein EHOMO(H) > EHOMO(D).
In a further embodiment, the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy ELUMO(H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy ELUMO(D), wherein ELUMO(H)
Figure imgf000027_0001
In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy EHOMO(H) and a lowest unoccupied molecular orbital LUMO(H) having an energy ELUMO(H), and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy EHOMO(D) and a lowest unoccupied molecular orbital LUMO(D) having an energy ELUMO(D), the organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy EHOMO(E) and a lowest unoccupied molecular orbital LUMO(E) having an energy ELUMO(E), wherein
EHOMO |_ > ^HOMO ) 3nd the difference between the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E (EHOMO(E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H (EHOMO(H)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV; and ELUMO |_ > ^LUMO ) 3nd the difference between the energy level of the lowest unoccupied molecular orbital LUMO(E) of the organic molecule according to the invention E (ELUMO(E)) and the lowest unoccupied molecular orbital LUMO(D) of the at least one further host compound D (ELUMO(D)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV.
In one embodiment of the invention the host compound D and/ or the host compound H is a thermally-activated delayed fluorescence (TADF)-material. TADF materials exhibit a AEST value, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), of less than 2500 crrr1. Preferably the TADF material exhibits a AEST value of less than 3000 cm-1, more preferably less than 1500 cm-1, even more preferably less than 1000 cm-1 or even less than 500 cm-1.
In one embodiment, the host compound D is a TADF material and the host compound FI exhibits a AEST value of more than 2500 cm-1. In a particular embodiment, the host compound D is a TADF material and the host compound FI is selected from group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9FI-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9FI-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9FI-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9FI-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9FI- carbazole.
In one embodiment, the host compound FI is a TADF material and the host compound D exhibits a AEST value of more than 2500 cm-1. In a particular embodiment, the host compound FI is a TADF material and the host compound D is selected from group consisting of T2T (2,4,6- tris(biphenyl-3-yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine) and/or TST (2,4,6-tris(9,9'-spirobifluorene-2-yl)-1,3,5-triazine).
In a further aspect, the invention relates to an optoelectronic device comprising an organic molecule or a composition of the type described here, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, more particularly gas and vapour sensors not hermetically externally shielded, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In one embodiment of the optoelectronic device of the invention, the organic molecule according to the invention E is used as emission material in a light-emitting layer EML.
In one embodiment of the optoelectronic device of the invention, the light-emitting layer EML consists of the composition according to the invention described here.
When the optoelectronic device is an OLED, it may, for example, have the following layer structure: 1. substrate
2. anode layer A
3. hole injection layer, HIL
4. hole transport layer, HTL
5. electron blocking layer, EBL
6. emitting layer, EML
7. hole blocking layer, HBL
8. electron transport layer, ETL
9. electron injection layer, EIL
10. cathode layer, wherein the OLED comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL only optionally, different layers may be merged and the OLED may comprise more than one layer of each layer type defined above.
Furthermore, the optoelectronic device may, in one embodiment, comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, for example, moisture, vapor and/or gases.
In one embodiment of the invention, the optoelectronic device is an OLED, with the following inverted layer structure:
1. substrate
2. cathode layer
3. electron injection layer, EIL
4. electron transport layer, ETL
5. hole blocking layer, HBL
6. emitting layer, B
7. electron blocking layer, EBL
8. hole transport layer, HTL
9. hole injection layer, HIL
10. anode layer A wherein the OLED comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL only optionally, different layers may be merged and the OLED may comprise more than one layer of each layer types defined above. In one embodiment of the invention, the optoelectronic device is an OLED, which may have a stacked architecture. In this architecture, contrary to the typical arrangement in which the OLEDs are placed side by side, the individual units are stacked on top of each other. Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs. Furthermore, the OLED exhibiting a stacked architecture may comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
In one embodiment of the invention, the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode. In particular, this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers. In a further embodiment, the emission layers are adjacently stacked. In a further embodiment, the tandem OLED comprises a charge generation layer between each two emission layers. In addition, adjacent emission layers or emission layers separated by a charge generation layer may be merged.
The substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow for a higher degree of flexibility. The anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs). Such anode layer A may, for example, comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
The anode layer A (essentially) may consist of indium tin oxide (ITO) (e.g., (ln03)o.9(Sn02)o.i). The roughness of the anode layer A caused by the transparent conductive oxides (TCOs) may be compensated by using a hole injection layer (HIL). Further, the HIL may facilitate the injection of quasi charge carriers (i.e. , holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) may comprise poly-3, 4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), M0O2, V2O5, CuPC or Cul, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL). The HIL may, for example, comprise PEDOT:PSS (poly-3, 4-ethylendioxy thiophene: polystyrene sulfonate), PEDOT (poly-3, 4-ethylendioxy thiophene), mMTDATA (4, 4', 4"- tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)- 9,9’-spirobifluorene), DNTPD (N1 ,NT-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m- tolylbenzene-1, 4-diamine), NPB (N,N'-nis-(1-naphthalenyl)-N,N'-bis-phenyl-(1 ,T-biphenyl)- 4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1 ,4,5,8,9,11- hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)- 9, 9'-spirobifluorene-2, 7-diamine).
Adjacent to the anode layer A or hole injection layer (HIL), a hole transport layer (HTL) is typically located. Herein, any hole transport compound may be used. For example, electron- rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound. The HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML. The hole transport layer (HTL) may also be an electron blocking layer (EBL). Preferably, hole transport compounds bear comparably high energy levels of their triplet states T1. For example, the hole transport layer (HTL) may comprise a star-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4- butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4 - cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4',4"-tris[2- naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT- CN and/or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). In addition, the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may, for example, be used as inorganic dopant. Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(l)pFBz) or transition metal complexes may, for example, be used as organic dopant.
The EBL may, for example, comprise mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-Butylphenyl)-3,6- bis(triphenylsilyl)-9H-carbazole), and/or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).
Adjacent to the hole transport layer (HTL), the light-emitting layer EML is typically located. The light-emitting layer EML comprises at least one light emitting molecule. Particularly, the EML comprises at least one light emitting molecule according to the invention E. In one embodiment, the light-emitting layer comprises only the organic molecules according to the invention. Typically, the EML additionally comprises one or more host materials H. For example, the host material H is selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2- yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3- yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine) and/or TST (2,4,6-tris(9,9'- spirobifluorene-2-yl)-1 ,3,5-triazine). The host material H typically should be selected to exhibit first triplet (T1) and first singlet (S1) energy levels, which are energetically higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.
In one embodiment of the invention, the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one light emitting organic molecule according to the invention and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole as hole-dominant host. In a further embodiment the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 % by weight, preferably 15-30 % by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
Adjacent to the light-emitting layer EML, an electron transport layer (ETL) may be located. Herein, any electron transporter may be used. Exemplarily, electron-poor compounds such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole), phosphinoxides and sulfone, may be used. An electron transporter may also be a star-shaped heterocycle such as 1, 3, 5-tri(1 -phenyl-1 H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3- yl)phenyl]benzene) and/or BTB (4, 4'-bis-[2-(4,6-diphenyl-1 , 3, 5-triazinyl)]-1,1 -biphenyl). Optionally, the ETL may be doped with materials such as Liq. The electron transport layer (ETL) may also block holes or a holeblocking layer (HBL) is introduced.
The HBL may, for example, comprise BCP (2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline = Bathocuproine), BAIq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (Aluminum-tris(8- hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T (2,4,6- tris(biphenyl-3-yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine), TST (2,4,6- tris(9,9'-spirobifluorene-2-yl)-1 ,3,5-triazine), and/or TCB/TCP (1 ,3,5-tris(N-carbazolyl)benzol/ 1 ,3,5-tris(carbazol)-9-yl) benzene).
Adjacent to the electron transport layer (ETL), a cathode layer C may be located. The cathode layer C may, for example, comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist of (essentially) intransparent metals such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscalic silver wires.
An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)). This layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8- hydroxyquinolinolatolithium), LhO, BaF2, MgO and/or NaF.
Optionally, the electron transport layer (ETL) and/or a hole blocking layer (HBL) may also comprise one or more host compounds H.
In order to modify the emission spectrum and/or the absorption spectrum of the light-emitting layer EM L further, the light-emitting layer EM L may further comprise one or more further emitter molecules F. Such an emitter molecule F may be any emitter molecule known in the art. Preferably such an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention E. The emitter molecule F may optionally be a TADF emitter. Alternatively, the emitter molecule F may optionally be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML. Exemplarily, the triplet and/or singlet excitons may be transferred from the organic emitter molecule according to the invention to the emitter molecule F before relaxing to the ground state SO by emitting light typically red- shifted in comparison to the light emitted by an organic molecule. Optionally, the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
Optionally, an optoelectronic device (e.g., an OLED) may, for example, be an essentially white optoelectronic device. For example, such white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more molecules as described above.
As used herein, if not defined more specifically in the particular context, the designation of the colors of emitted and/or absorbed light is as follows: violet: wavelength range of >380-420 nm; deep blue: wavelength range of >420-480 nm; sky blue: wavelength range of >480-500 nm; green: wavelength range of >500-560 nm; yellow: wavelength range of >560-580 nm; orange: wavelength range of >580-620 nm; red: wavelength range of >620-800 nm.
With respect to emitter molecules, such colors refer to the emission maximum. Therefore, for example, a deep blue emitter has an emission maximum in the range of from >420 to 480 nm, a sky blue emitter has an emission maximum in the range of from >480 to 500 nm, a green emitter has an emission maximum in a range of from >500 to 560 nm, a red emitter has an emission maximum in a range of from >620 to 800 nm.
A deep blue emitter may preferably have an emission maximum of below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.
Accordingly, a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m2 of more than 8 %, more preferably of more than 10 %, more preferably of more than 13 %, even more preferably of more than 15 % or even more than 20 % and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/nT of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h. Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.
A further aspect of the present invention relates to an OLED, which emits light at a distinct color point. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light with a FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV or even less than 0.17 eV.
A further aspect of the present invention relates to an OLED, which emits light with Cl Ex and CIEy color coordinates close to the CIEx (= 0.131) and CIEy (= 0.046) color coordinates of the primary color blue (CIEx = 0.131 and CIEy = 0.046) as defined by ITU-R Recommendation BT.2020 (Rec. 2020) and thus is suited for the use in Ultra High Definition (UHD) displays, e.g. UHD-TVs. Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a Cl Ey color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
In a further aspect, the invention relates to a method for producing an optoelectronic component. In this case an organic molecule of the invention is used.
The optoelectronic device, in particular the OLED according to the present invention can be fabricated by any means of vapor deposition and/ or liquid processing. Accordingly, at least one layer is prepared by means of a sublimation process, prepared by means of an organic vapor phase deposition process, prepared by means of a carrier gas sublimation process, solution processed or printed. The methods used to fabricate the optoelectronic device, in particular the OLED according to the present invention are known in the art. The different layers are individually and successively deposited on a suitable substrate by means of subsequent deposition processes. The individual layers may be deposited using the same or differing deposition methods.
Vapor deposition processes, for example, comprise thermal (co) evaporation, chemical vapor deposition and physical vapor deposition. For active matrix OLED display, an AMOLED backplane is used as substrate. The individual layer may be processed from solutions or dispersions employing adequate solvents. Solution deposition process, for example, comprise spin coating, dip coating and jet printing. Liquid processing may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may be completely or partially removed by means known in the state of the art.
Examples
General synthesis scheme I
General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention wherein Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI:
Figure imgf000037_0001
Alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to I3.
Figure imgf000038_0001
Alternatively, the corresponding boronic acid derivative of substrate 13 might be used as starting material under the same conditions.
Alternative one-pot ring closure scheme directly converting 12 to P1.
Figure imgf000038_0002
General procedure for synthesis A A V1 :
Figure imgf000039_0001
E1 E2 R v 11
E1 (1.00 equivalents), E2 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(¾u)3, CAS: 13716-12-6 , 0.04 equivalents) and sodium tert-butoxide (NaO¾u; 1.70 equivalents) are stirred under nitrogen atmosphere in toluene at 80 °C for 1-16 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and water and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and 11 is obtained as solid or an oil.
General procedure for synthesis A A V2.
Figure imgf000039_0002
11 (2.20 equivalents), E3 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium Pd2(dba)3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (0.08 equivalents, P(¾u)3, CAS: 13716-12-6) and sodium tert-butoxide (NaO¾u; 3.30 equivalents) are stirred under nitrogen atmosphere in toluene at 110 °C for 1-16 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and water and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I2 is obtained as solid.
General procedure for synthesis A A V3. Under nitrogen atmosphere 12 (1.00 equivalent) is dissolved in dry THF. The resulting solution is cooled down to -10 °C. Subsequently, tert- BuLi (2.20 equivalents, CAS: 594-19-4) is slowly added and stirring is continued at 0 °C. After complete lithiation, 1,3,2-dioxaborolane (3.00 equivalents, CAS: 61676-62-8 or alternatively trimethyl borate, CAS 121-43-7) is added, followed by heating at 40 °C for 2 h. After cooling down to room temperature (rt), water is added and the phases separated. The combined organic layers are dried over MgSCU, filtered and concentrated under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography to yield I3 or the corresponding boronic acid, respectively, as solid.
Figure imgf000040_0001
I3 (1.00 equivalent), N,N-diisopropylethylamine (10 equivalents, CAS: 7087-68-5) and AlC (10 equivalents, CAS: 7446-70-0) are stirred under nitrogen atmosphere in chlorobenzene at 120°C for 4 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and water and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid. General procedure for synthesis A A V5.
Figure imgf000041_0001
I2 5 h P1
12 (1.00 equivalents) is dissolved in tert-butylbenzene under nitrogen atmosphere and the solution is cooled to -30°C. A solution of tert-butyllithium (‘BuLi) (2.20 equivalents, CAS: 594- 19-4) is added dropwise and the reaction mixture is allowed to warm up to 0 °C. After stirring for 120 minutes at 60°C, the solvent of the ‘BuLi -solution and byproducts are removed under reduced pressure and the reaction mixture is cooled again to -30 °C. A solution of boron tribromide (BBr3, CAS: 10294-33-4, 2.20 equivalents) is added dropwise, the cooling bath is removed and the reaction mixture is allowed to warm to room temperature (rt). After stirring for 30 minutes at rt, the reaction mixture is cooled to 0 °C and N,N-diisopropylethylamine (CAS: 7087-68-5, 3.00 equivalents) is added. The reaction mixture is allowed to warm to rt and then heated at reflux at 120 °C for 3h. Subsequently, the reaction mixture is poured into water and the resulting precipitate is filtered and washed with a minimum amount of ethyl acetate to obtain P1 as a solid product. P1 can be further purified by recrystallization or by flash chromatography.
General Synthesis Scheme II
General synthesis scheme II provides a synthesis scheme for organic molecules according to the invention, wherein Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI:
Figure imgf000041_0002
Alternative one-pot procedure to convert I5 into P2. E3 (1.00 equivalents), E1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(¾u)3, CAS: 13716-12-6 , 0.04 equivalents) and sodium tert-butoxide (NaO¾u; 3.30 equivalents) are stirred under nitrogen atmosphere in toluene at 80 °C for 1-16 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and water and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I4 is obtained as solid or an oil.
General procedure for synthesis A A V7
Figure imgf000043_0001
I4 15 14 (1.00 equivalents), E2.2 (2.20 equivalents), tris(dibenzylideneacetone)-dipalladium Pd2(dba)3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (0.08 equivalents, P(¾u)3, CAS: 13716-12-6) and sodium tert-butoxide (NaO¾u; 3.30 equivalents) are stirred under nitrogen atmosphere in toluene at 110 °C for 1-16 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and water and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I5 is obtained as solid.
Figure imgf000044_0001
Boronic acid ester 16 is obtained according to AAV3 using compound 15 as the starting material. Alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 16.
Figure imgf000044_0002
Target compound P2 is synthesized according to AAV4 using boronic acid ester I6 as the starting material. Alternatively, the boronic acid corresponding to I6 can be used as the starting material for the synthesis of P2.
Alternative one-pot procedure to convert 15 into P2. The synthesis of the target P2 is conducted via a one-pot protocol, where the chloride precursor I5 is directly converted into P2 following the procedure described within AAV5.
General Synthesis Scheme III
General synthesis scheme III provides a synthesis scheme for organic molecules according to the invention where the limitations of scheme I and II (i.e. Rx = R1, RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI) do not apply.
Figure imgf000045_0001
The synthesis of compound 17.1 is carried out following the procedure described under AAV1 , using E2.2 (1.1 equivalents) and amine E1 as the reactants.
Figure imgf000045_0002
The synthesis of compound 17.2 is carried out following the procedure described under AAV1 , using E2.2 (1.1 equivalents) and amine E1 as the reactants. Compound I8 is synthesized according to AAV8.
Figure imgf000046_0002
Compound I9 is synthesized according to AAV9.
Figure imgf000046_0001
The synthesis of boronicacid ester 110 is carried out as described within AAV3 using precursor I9 as the substrate. Alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 110. Target compound P3 is synthesized according to AAV4 using boronic acid ester 110 as the starting material. Alternatively, the boronic acid corresponding to 110 might be used as the starting material for the synthesis of P3.
Alternative one-pot procedure to convert 19 into P3.
Figure imgf000047_0001
The synthesis of the target P3 is conducted via a one-pot protocol, where the chloride precursor 19 is directly converted into P3 following the procedure described within AAV5.
General procedure for synthesis A A V8.
Figure imgf000047_0002
18
E3.2 (1.10 equivalents), 17.1 (1.00 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(¾u)3, CAS: 13716- 12-6, 0.04 equivalents) and sodium tert-butoxide (NaO¾u; 1.70 equivalents) are stirred under nitrogen atmosphere in toluene at 80 °C for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and 18 is obtained as solid.
General procedure for synthesis A A V9.
Figure imgf000048_0001
17.2 (1.10 equivalents), I8 (1.00 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(¾u)3, CAS: 13716-12-6 , 0.04 equivalents) and sodium tert-butoxide (NaO¾u; 1.70 equivalents) are stirred under nitrogen atmosphere in toluene at 110 °C for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I9 is obtained as solid.
General Synthesis Scheme IV
General synthesis scheme IV provides a synthesis scheme for organic molecules according to the invention, wherein Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI:
Figure imgf000048_0002
The synthesis of dichloro derivative I2-CI is performed as described within AAV2, starting from 1 ,3-Dibromo-2, 5-dichlorobenzene (1.0 equivalents, CAS: 81067-41-6) and amine I2. Boronic ester I3-CI is synthesized from I2-CI following the procedure of AAV3, wherein alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to I3-CI.
Figure imgf000049_0001
The para- chloro derivative P1-CI is synthesized from P1-CI as described within AAV4. Alternatively, under the same conditions, the corresponding boronic acid derivative of substrate I3-CI might be used as starting material yielding P1-CI.
Alternative one-pot ring closure scheme directly converting I2-CI to P1-CI.
Figure imgf000049_0002
12-CI 5 h P1-CI
The one-pot synthesis of P1-CI starting from I2-CI is carried out as described within AAV5. General procedure for synthesis AAV10. Under nitrogen atmosphere compound P1-CI (1.0 equivalent), boronic acid Rv-B(OH)2 (6.0 equivalents), Palladium-(ll)-acetate (0.06 equivalents, CAS: 3375-31-3), X-Phos (0.24 equivalents, CAS: 564483-18-7) and tribasic potassium phosphate (9.0 equivalents, CAS: 7778-53-2) are stirred in a mixture of toluene and dioxane (1:1) at 100 °C for 1 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and water and the phases are separated. The combined organic layers are treated with activated charcoal for 10 min, followed by filtration through a pad of Celite® (kieselgur). The filtrate is dried over MgSCU and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid.
General Synthesis Scheme V
General synthesis scheme V provides a synthesis scheme for organic molecules according to the invention, wherein Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI:
Figure imgf000050_0001
Compound I4-CI was synthesized accordingly to procedure AAV6 where 1,3-dibromo-2,5- dichlorobenzene (1.0 equivalent, CAS 81067-41-6) and primary amine E1 were used as the reactants. Compound 15-CI is obtained by following the procedure AAV7 using secondary bisamine 14-CI and 1-bromo-3,5-diphenylbenzene (CAS: 103068-20-8) as the reactants.
Figure imgf000051_0001
Boronic acid ester 16-CI is obtained according to AAV3 using compound 15-CI as the starting material. Alternatively, under the same conditions, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 16-CI.
Figure imgf000051_0002
The synthesis of P2-CI is conducted as described in AAV5 using I5-CI as the substrate. The target material P2 is synthesized as described in AAV10 using P2-CI as the starting material.
General Synthesis Scheme VI
General synthesis scheme VI provides a synthesis scheme for organic molecules according to the invention where the limitations of scheme I and II (i.e. Rx = R', RIX = R", Rvm = Rm, RVM = RIV, and Rv = RVI) do not apply.
Figure imgf000052_0001
Compound I8-CI is synthesized as described within AAV8, where 1-bromo-2, 3,5- trichlorobenzene (1.0 equivalent) and primary amine 17.1 were used as the reactants.
Figure imgf000052_0002
Compound I9-CI is synthesized from I7.2 and I8-CI according to AAV9. The synthesis of boronic acid ester 110-CI is carried out as described within AAV3 using precursor I9-CI as the substrate. Alternatively, trimethyl borate may be used as borylating reagent yielding the boronic acid derivatives corresponding to 110-CI.
Figure imgf000053_0001
Compound P3-CI is synthesized according to AAV4 using boronic acid ester 110-CI as the starting material. Alternatively, the boronic acid corresponding to 110-CI might be used as the starting material for the synthesis of P3-CI.
Alternative one-pot procedure to convert I9-CI into P3-CI.
Figure imgf000053_0002
The synthesis of P3-CI is conducted as described in AAV5 using I9-CI as the substrate.
The target material P3 is synthesized as described in AAV10 using P3-CI as the starting material.
Cyclic voltammetry
Cyclic voltammograms are measured from solutions having concentration of 103 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).
Density functional theory calculation
Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (Rl). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.
Photophysical measurements
Sample pretreatment: Spin-coating Apparatus: Spin150, SPS euro.
The sample concentration is 10 mg/ml, dissolved in a suitable solvent.
Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are dried at 70 °C for 1 min.
Photoluminescence spectroscopy and Time-Correlated Single-Photon Counting (TCSPC) Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.
Excitation sources:
NanoLED 370 (wavelength: 371 nm, puls duration: 1,1 ns)
NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)
SpectraLED 310 (wavelength: 314 nm)
SpectraLED 355 (wavelength: 355 nm). Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.
Photoluminescence quantum yield measurements
For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system ( Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.
Emission maxima are given in nm, quantum yields F in % and CIE coordinates as x,y values. PLQY is determined using the following protocol:
1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference
2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength
3) Measurement
Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:
Figure imgf000056_0001
wherein nPhoton denotes the photon count and Int. the intensity.
Production and characterization of optoelectronic devices
Optoelectronic devices, in particular OLED devices, comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80 % of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95 % of the initial luminance etc. Accelerated lifetime measurements are performed (e.g. applying increased current densities). For example, LT80 values at 500 cd/m2 are determined using the following equation:
Figure imgf000056_0002
wherein Lo denotes the initial luminance at the applied current density.
The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
HPLC-MS
HPLC-MS analysis is performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).
Exemplarly a typical HPLC method is as follows: a reverse phase column 4,6mm x 150mm, particle size 3,5 pm from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6 x 150 mm, 3.5 pm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients
Flow rate [ml/min] Time [min] A[%] B[%] C[%]
2.5 0 40 50 10
2.5 5 40 50 10
2.5 25 10 20 70
2.5 35 10 20 70
2.5 35.01 40 50 10
2.5 40.01 40 50 10
2.5 41.01 40 50 10 using the following solvent mixtures:
Figure imgf000057_0001
An injection volume of 5 pL from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.
Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI +) or negative (APCI -) ionization mode. Example 1
Figure imgf000058_0001
Example 1 was synthesized according to
AAV1 (49% yield), wherein 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) as E1;
AAV2 (42% yield), wherein 1,3-dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E3; and A A V5 (48% yield).
MS (HPLC-MS, APCI, pos. ionization), m/z (retention time): 781.6 (6.16 min).
The emission maximum of example 1 (2% by weight in PMMA) is at 464 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.12 and the PLQY is 73%. The onset of the emission spectrum is determined at 2.79 eV.
Example 2
Figure imgf000058_0002
AAV1 (49% yield), wherein 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) as E1; AAV2 (69% yield), wherein 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) was used as reactant E3; and AAV5 (13% yield).
MS (HPLC-MS, APPI, pos. ionization), m/z (retention time): 795.6 (6.26 min).
The emission maximum of example 2 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.11 and the PLQY is 76%. The onset of the emission spectrum is determined at 2.79 eV.
Example 3
Figure imgf000059_0001
Example 1 was synthesized according to
AAV2 (83% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) and 4,4'- bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and 11, respectively;
AAV3 (32% yield), wherein trimethyl borate (CAS 121-43-7) was used as the borylating reagent and wherein the corresponding boronic acid derivative of I3 was obtained; and AAV4 (23% yield).
MS (HPLC-MS, APPI, pos. ionization), m/z (retention time): 893.7 (7.66 min).
The emission maximum of example 3 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.16 eV, the CIEy coordinate is 0.10 and the PLQY is 80%. The onset of the emission spectrum is determined at 2.79 eV. Example 4
Figure imgf000060_0001
Example 4 was synthesized according to
AAV2 (72% yield), wherein 4-Chloro-3,5-dibromotoluene (CAS 202925-05-1) and 4,4'- bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and 11, respectively;
AAV3 (50% yield), wherein trimethyl borate (CAS 121-43-7) was used as the borylating reagent and wherein the corresponding dichloride I2-CI was used as the reactant and wherein the corresponding boronic acid derivative of I3-CI was obtained;
AAV4 (58% yield); and AAV10 (81% yield), wherein the corresponding starting material P1-CI was reacted with methaneboronic acid (CAS: 13061-96-6).
MS (HPLC-MS), m/z (retention time): 907.80 (7.68 min).
The emission maximum of example 4 (2% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.10 and the PLQY is 81%. The onset of the emission spectrum is determined at 2.81 eV.
Example D1
Example 1 was tested in the OLED D1 , which was fabricated with the following layer structure:
Figure imgf000061_0002
Figure imgf000061_0001
MAT1 MAT2
MAT3 MAT4
OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m2 of 12.1%. The emission maximum is at 468 nm with a FWHM of 26 nm at 3.6 V. The corresponding CIEy value is 0.12.
Example D2
Example 2 was tested in the OLED D2, which was fabricated with the following layer structure:
Figure imgf000062_0001
OLED D2 yielded an external quantum efficiency (EQE) at 1000 cd/m2 of 10.9%. The emission maximum is at 464 nm with a FWHM of 28 nm at 3.8 V. The corresponding CIEy value is 0.10. Example D3
Example 3 was tested in the OLED D3, which was fabricated with the following layer structure:
Figure imgf000063_0001
OLED D3 yielded an external quantum efficiency (EQE) at 1000 cd/m2 of 11.8%. The emission maximum is at 466 nm with a FWHM of 26 nm at 3.5 V. The corresponding CIEy value is 0.10.
Example D4
Example 4 was tested in the OLED D4, which was fabricated with the following layer structure:
Figure imgf000063_0002
OLED D4 yielded an external quantum efficiency (EQE) at 1000 cd/m2 of 11.2%. The emission maximum is at 464 nm with a FWHM of 26 nm at 3.6 V. The corresponding CIEy value is 0.09.
Additional Examples of Organic Molecules of the Invention
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000070_0001
Figure imgf000071_0001

Claims

Claims
1. Organic molecule, comprising a structure of formula I:
Figure imgf000072_0002
Formula I wherein either both T are R1 or both V are R1 while the group T or V that is not R1 is selected from the group consisting of hydrogen, deuterium;
Ci-C5-alkyl; and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph; wherein
R1 comprises or consists of a structure of formula F
Figure imgf000072_0001
Formula F wherein n is an integer, which is at each occurrence selected from the group consisting of 0, 1 , 2, 3, 4 and 5; and the dotted line representing the position at which it is bonded to the structure shown in formula I;
R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium, CrCs-alkyl;
R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of: R1, hydrogen, deuterium,
N(R5)2,
OR5,
SR5,
Si(R5)s,
B(OR5)2,
OSO2R5,
CFs,
CN, halogen,
CrC4o-alkyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C40-thioalkoxy, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl, which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5; Ce-Ceo-aryl, which is optionally substituted with one or more substituents R5; and C3-C57-heteroaryl, which is optionally substituted with one or more substituents R5;
R5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(Ci-C5-alkyl)3, Si(Ph)3,
Ci-C5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-C5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-C5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C6-Ci8-aryl, which is optionally substituted with one or more CrCs-alkyl substituents;
C3-C17-heteroaryl, which is optionally substituted with one or more CrCs-alkyl substituents; N(C6-Ci8-aryl)2,
N(C3-Ci7-heteroaryl)2; and N(C3-Ci7-heteroaryl)(C6-Ci8-aryl); and
RXI is selected from the group consisting of hydrogen, deuterium, chloride and C1-C5 alkyl.
2. Organic molecule according to claim 1, wherein R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of:
R1, hydrogen, deuterium, halogen, Me, 'Pr, ‘Bu, CN, CF3, SiMe3, SiPhb, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, CN, CF3, and Ph, and N(Ph)2.
3. Organic molecule according to any of claims 1 or 2, wherein T and V are selected from the group consisting of
R1; hydrogen, deuterium, Me, 'Pr, ‘Bu, and
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph.
4. Organic molecule according to any of claims 1 to 3, wherein R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen, deuterium,
Me, 'Pr, ‘Bu, and neo-pentyl.
5. Organic molecule according to any of claims 1 to 4, wherein R6 is at each occurrence independently from each other selected from the group consisting of: hydrogen and Me.
6. Organic molecule according to any of claims 1 to 5, wherein R', R", Rm, RIV, Rv, RVI, RVM, Rvm, RIX and Rx is independently from another selected from the group consisting of: R1, hydrogen, deuterium, Me, 'Pr, ‘Bu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ‘Bu, and Ph, and N(Ph)2.
7. Organic molecule according to any of claims 1 or 6, comprising a structure of formula II: Formula II.
8. Organic molecule according to any of claims 1 to 7, wherein R', R", Rm and RIV is independently from another selected from the group consisting of: hydrogen, Me, ‘Bu, and Ph.
9. Organic molecule according to any of claims 1 to 8, wherein RXI is selected from the group consisting of hydrogen, Me, 'Pr and ‘Bu.
10. Use of an organic molecule according to any of claims 1 to 9 as a luminescent emitter in an optoelectronic device.
11. Use according to claim 10, wherein the optoelectronic device is selected from the group consisting of:
• organic light-emitting diodes (OLEDs),
• light-emitting electrochemical cells,
• OLED-sensors,
• organic diodes,
• organic solar cells,
• organic transistors,
• organic field-effect transistors,
• organic lasers, and
• down-conversion elements.
12. Composition, comprising:
(a) an organic molecule according to any of claims 1 to 9, in particular in the form of an emitter and/or a host, and
(b) an emitter and/or a host material, which differs from the organic molecule, and
(c) optionally, a dye and/or a solvent.
13. Optoelectronic device, comprising an organic molecule according to any of claims 1 to 9 or a composition according to claim 12, in particular in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.
14. Optoelectronic device according to claim 13, comprising:
- a substrate,
- an anode, and
- a cathode, wherein the anode or the cathode is disposed on the substrate, and
- a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule or the composition.
15. Method for producing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 9 ora composition according to claim 12 is used, in particular comprising the processing of the organic molecule by a vacuum evaporation method or from a solution.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3967699A1 (en) * 2020-09-15 2022-03-16 Samsung Electronics Co., Ltd. Polycyclic compound and organic light-emitting device including the same

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200176679A1 (en) * 2017-05-22 2020-06-04 Material Science Co., Ltd. Organic compound and organic electroluminescent device comprising the same
WO2020184834A1 (en) * 2019-03-08 2020-09-17 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising same
WO2021020943A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light-emitting device
WO2021020947A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light-emitting device
WO2021020941A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light emitting device
WO2021049889A1 (en) * 2019-09-10 2021-03-18 주식회사 엘지화학 Compound and organic light-emitting device comprising same
WO2021073385A1 (en) * 2019-10-18 2021-04-22 北京鼎材科技有限公司 Boron-containing compound and organic electroluminescent device containing same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200176679A1 (en) * 2017-05-22 2020-06-04 Material Science Co., Ltd. Organic compound and organic electroluminescent device comprising the same
WO2020184834A1 (en) * 2019-03-08 2020-09-17 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising same
WO2021020943A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light-emitting device
WO2021020947A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light-emitting device
WO2021020941A1 (en) * 2019-07-31 2021-02-04 주식회사 엘지화학 Organic light emitting device
WO2021049889A1 (en) * 2019-09-10 2021-03-18 주식회사 엘지화학 Compound and organic light-emitting device comprising same
WO2021073385A1 (en) * 2019-10-18 2021-04-22 北京鼎材科技有限公司 Boron-containing compound and organic electroluminescent device containing same

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CAS , no. 202925-05-1
CAS, no. 103068-20-8
LEE S U: "Preparation of fused boron-containing polycyclic compounds for organic electroluminescent device", US2020176679 A1, 4 June 2020 (2020-06-04), pages 1 - 9, XP055835074 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3967699A1 (en) * 2020-09-15 2022-03-16 Samsung Electronics Co., Ltd. Polycyclic compound and organic light-emitting device including the same

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